data_cs001 _audit_creation_date 2012-11-28 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:22:26, GUI svn.r4372) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H16 Cl N3 O' _chemical_formula_sum 'C16 H16 Cl N3 O' _chemical_formula_weight 301.77 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C16 H17 N3 O1 Cl1' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system 'orthorhombic' _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 7.20516(13) _cell_length_b 10.1306(2) _cell_length_c 19.4721(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1421.32(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4345 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 74.8513 _cell_measurement_theta_min 4.3605 _exptl_absorpt_coefficient_mu 2.395 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_correction_T_min 0.889 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.2609 _exptl_crystal_size_mid 0.1869 _exptl_crystal_size_min 0.0724 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_unetI/netI 0.0267 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 6527 _diffrn_reflns_theta_full 72.02 _diffrn_reflns_theta_max 72.02 _diffrn_reflns_theta_min 4.92 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 10.4839 _diffrn_measured_fraction_theta_full 0.9946 _diffrn_measured_fraction_theta_max 0.9946 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -53.00 29.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -43.5000 48.0000 122.0000 82 #__ type_ start__ end____ width___ exp.time_ 2 omega -46.00 -9.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -43.5000 48.0000 26.0000 37 #__ type_ start__ end____ width___ exp.time_ 3 omega 40.00 66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 -48.0000 -26.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega 84.00 170.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 48.0000 -153.0000 86 #__ type_ start__ end____ width___ exp.time_ 5 omega 43.00 69.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 -48.0000 -122.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega 83.00 178.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 48.0000 -57.0000 95 #__ type_ start__ end____ width___ exp.time_ 7 omega 50.00 96.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 41.6798 -125.0000 -180.0000 46 #__ type_ start__ end____ width___ exp.time_ 8 omega -119.00 -84.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -43.5000 -94.0000 -120.0000 35 #__ type_ start__ end____ width___ exp.time_ 9 omega -125.00 -81.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -43.5000 -94.0000 150.0000 44 #__ type_ start__ end____ width___ exp.time_ 10 omega -125.00 -98.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -43.5000 -94.0000 120.0000 27 #__ type_ start__ end____ width___ exp.time_ 11 omega 34.00 63.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 -30.0000 -90.0000 29 #__ type_ start__ end____ width___ exp.time_ 12 omega 34.00 70.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 -30.0000 30.0000 36 #__ type_ start__ end____ width___ exp.time_ 13 omega 37.00 102.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 -94.0000 90.0000 65 #__ type_ start__ end____ width___ exp.time_ 14 omega 34.00 87.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 -30.0000 -60.0000 53 #__ type_ start__ end____ width___ exp.time_ 15 omega 37.00 63.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 -30.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 16 omega 48.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 109.1316 -45.0000 -180.0000 43 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0679083000 _diffrn_orient_matrix_UB_12 0.0599246000 _diffrn_orient_matrix_UB_13 -0.0682526000 _diffrn_orient_matrix_UB_21 0.1623681000 _diffrn_orient_matrix_UB_22 -0.0668730000 _diffrn_orient_matrix_UB_23 -0.0380010000 _diffrn_orient_matrix_UB_31 -0.1213565000 _diffrn_orient_matrix_UB_32 -0.1227349000 _diffrn_orient_matrix_UB_33 -0.0125754000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2637 _reflns_number_total 2728 _reflns_odcompleteness_completeness 99.46 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 71.98 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.160 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.001(11) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2728 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0273 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.1506P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0705 _refine_ls_wR_factor_ref 0.0716 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H5 of C5, H8 of C8, H13 of C13, H11 of C11, {H15A,H15B} of C15, {H4A,H4B} of C4, H9 of C9, {H14A,H14B} of C14, {H16A,H16B} of C16, H10 of C10 2. Restrained distances N1-H1 0.88 with sigma of 0.01 N2-H2 0.88 with sigma of 0.01 3.a Ternary CH refined with riding coordinates and stretchable bonds: C5(H5), C13(H13) 3.b Secondary CH2 refined with riding coordinates and stretchable bonds: C4(H4A,H4B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B) 3.c Aromatic/amide H refined with riding coordinates and stretchable bonds: C8(H8), C9(H9), C10(H10), C11(H11) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0242(2) 0.04871(15) 0.20759(8) 0.0199(3) Uani 1 1 d . . . C2 C 0.0160(2) 0.01302(14) 0.28052(8) 0.0181(3) Uani 1 1 d . . . C3 C -0.1117(2) 0.02102(15) 0.33188(9) 0.0218(3) Uani 1 1 d . . . C4 C -0.3065(2) 0.06648(18) 0.31936(9) 0.0276(4) Uani 1 1 d . . . H4A H -0.3236(3) 0.1546(13) 0.3378(3) 0.033 Uiso 1 1 calc R . . H4B H -0.3934(13) 0.0076(9) 0.3420(4) 0.033 Uiso 1 1 calc R . . C5 C -0.3418(2) 0.06692(17) 0.24182(9) 0.0262(3) Uani 1 1 d . . . H5 H -0.455(2) 0.1198(11) 0.23364(19) 0.031 Uiso 1 1 calc R . . C6 C 0.1567(2) -0.06825(15) 0.37303(7) 0.0212(3) Uani 1 1 d . . . C7 C -0.0236(2) -0.02963(15) 0.39231(8) 0.0223(3) Uani 1 1 d . . . C8 C 0.2819(3) -0.12293(16) 0.42010(8) 0.0280(4) Uani 1 1 d . . . H8 H 0.406(3) -0.1511(6) 0.4061(3) 0.034 Uiso 1 1 calc R . . C9 C 0.2218(3) -0.13522(18) 0.48761(8) 0.0357(4) Uani 1 1 d . . . H9 H 0.306(2) -0.1726(10) 0.5219(9) 0.043 Uiso 1 1 calc R . . C10 C 0.0445(3) -0.09567(19) 0.50787(9) 0.0383(5) Uani 1 1 d . . . H10 H 0.0082(10) -0.1040(3) 0.5557(12) 0.046 Uiso 1 1 calc R . . C11 C -0.0803(3) -0.04478(18) 0.46088(9) 0.0323(4) Uani 1 1 d . . . H11 H -0.208(3) -0.0193(6) 0.4754(3) 0.039 Uiso 1 1 calc R . . C12 C -0.3764(2) -0.07046(17) 0.21233(9) 0.0238(3) Uani 1 1 d . . . C13 C -0.0521(2) -0.07557(16) 0.16383(8) 0.0194(3) Uani 1 1 d . . . H13 H 0.0365(17) -0.1449(13) 0.1803(3) 0.023 Uiso 1 1 calc R . . C14 C -0.2849(2) -0.22401(17) 0.12089(9) 0.0254(3) Uani 1 1 d . . . H14A H -0.4174(18) -0.2114(2) 0.1019(3) 0.031 Uiso 1 1 calc R . . H14B H -0.2725(3) -0.3184(13) 0.1403(3) 0.031 Uiso 1 1 calc R . . C15 C -0.1383(2) -0.19796(17) 0.06479(8) 0.0256(3) Uani 1 1 d . . . H15A H -0.0480(13) -0.2720(11) 0.06245(9) 0.031 Uiso 1 1 calc R . . H15B H -0.1985(9) -0.1880(2) 0.0191(7) 0.031 Uiso 1 1 calc R . . C16 C -0.0401(2) -0.06897(17) 0.08579(8) 0.0248(3) Uani 1 1 d . . . H16A H 0.0896(18) -0.06755(18) 0.0700(2) 0.030 Uiso 1 1 calc R . . H16B H -0.1053(9) 0.0089(11) 0.0677(3) 0.030 Uiso 1 1 calc R . . Cl1 Cl 0.16626(5) 0.14410(4) 0.173218(18) 0.02646(11) Uani 1 1 d . . . N1 N -0.19046(19) 0.12920(14) 0.20280(7) 0.0266(3) Uani 1 1 d D . . N2 N 0.17847(18) -0.04309(13) 0.30384(6) 0.0190(3) Uani 1 1 d D . . N3 N -0.24280(17) -0.12508(13) 0.17374(7) 0.0216(3) Uani 1 1 d . . . O1 O -0.52888(15) -0.12541(12) 0.22044(7) 0.0303(3) Uani 1 1 d . . . H2 H 0.2794(18) -0.0589(18) 0.2796(9) 0.024(5) Uiso 1 1 d D . . H1 H -0.168(3) 0.2095(12) 0.2166(11) 0.041(6) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0168(7) 0.0214(7) 0.0215(7) 0.0036(6) 0.0006(6) 0.0004(6) C2 0.0159(6) 0.0179(7) 0.0204(7) -0.0001(6) 0.0015(6) 0.0003(6) C3 0.0223(7) 0.0200(7) 0.0230(7) -0.0037(6) 0.0044(6) -0.0007(6) C4 0.0198(7) 0.0295(8) 0.0334(9) -0.0100(7) 0.0055(7) 0.0021(7) C5 0.0159(7) 0.0254(8) 0.0373(9) -0.0054(7) -0.0007(7) 0.0054(7) C6 0.0296(8) 0.0163(7) 0.0176(7) -0.0020(6) -0.0017(6) -0.0012(7) C7 0.0296(8) 0.0179(7) 0.0194(7) -0.0035(6) 0.0048(6) -0.0046(7) C8 0.0397(10) 0.0212(8) 0.0232(7) 0.0002(7) -0.0081(7) -0.0007(7) C9 0.0622(12) 0.0252(9) 0.0196(8) 0.0008(7) -0.0112(8) -0.0058(9) C10 0.0669(14) 0.0332(10) 0.0150(7) 0.0005(7) 0.0035(9) -0.0142(10) C11 0.0449(10) 0.0281(9) 0.0240(8) -0.0052(7) 0.0112(8) -0.0091(8) C12 0.0167(7) 0.0249(8) 0.0298(8) -0.0017(7) -0.0009(6) 0.0029(6) C13 0.0162(7) 0.0229(7) 0.0191(7) 0.0018(6) 0.0009(6) 0.0023(6) C14 0.0237(8) 0.0239(8) 0.0287(8) -0.0050(7) 0.0005(6) -0.0006(6) C15 0.0285(8) 0.0251(8) 0.0231(7) -0.0010(6) 0.0006(7) 0.0022(7) C16 0.0275(8) 0.0277(8) 0.0190(7) 0.0016(6) -0.0019(6) -0.0012(7) Cl1 0.02793(19) 0.0300(2) 0.02142(16) 0.00558(16) 0.00004(15) -0.00852(16) N1 0.0232(6) 0.0215(7) 0.0350(7) 0.0029(6) -0.0014(6) 0.0062(6) N2 0.0164(6) 0.0233(6) 0.0173(6) 0.0005(5) 0.0009(5) 0.0028(5) N3 0.0166(6) 0.0224(6) 0.0258(6) -0.0017(6) 0.0014(5) 0.0007(5) O1 0.0171(5) 0.0335(6) 0.0403(6) -0.0086(6) 0.0050(5) -0.0008(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.494(2) . ? C1 C13 1.533(2) . ? C1 Cl1 1.8072(16) . ? C1 N1 1.4519(19) . ? C2 C3 1.362(2) . ? C2 N2 1.378(2) . ? C3 C4 1.497(2) . ? C3 C7 1.432(2) . ? C4 H4A 0.9703 . ? C4 H4B 0.9703 . ? C4 C5 1.531(2) . ? C5 H5 0.9906 . ? C5 C12 1.526(2) . ? C5 N1 1.471(2) . ? C6 C7 1.408(2) . ? C6 C8 1.400(2) . ? C6 N2 1.3802(19) . ? C7 C11 1.405(2) . ? C8 H8 0.9759 . ? C8 C9 1.390(2) . ? C9 H9 0.9792 . ? C9 C10 1.396(3) . ? C10 H10 0.9702 . ? C10 C11 1.383(3) . ? C11 H11 0.9993 . ? C12 N3 1.341(2) . ? C12 O1 1.242(2) . ? C13 H13 1.0018 . ? C13 C16 1.524(2) . ? C13 N3 1.4752(18) . ? C14 H14A 1.0321 . ? C14 H14B 1.0321 . ? C14 C15 1.542(2) . ? C14 N3 1.468(2) . ? C15 H15A 0.9943 . ? C15 H15B 0.9943 . ? C15 C16 1.541(2) . ? C16 H16A 0.9837 . ? C16 H16B 0.9837 . ? N1 H1 0.872(10) . ? N2 H2 0.881(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C13 110.79(12) . . ? C2 C1 Cl1 109.52(10) . . ? C13 C1 Cl1 109.44(10) . . ? N1 C1 C2 110.93(12) . . ? N1 C1 C13 108.50(13) . . ? N1 C1 Cl1 107.60(10) . . ? C3 C2 C1 123.55(14) . . ? C3 C2 N2 110.90(14) . . ? N2 C2 C1 125.30(13) . . ? C2 C3 C4 122.17(15) . . ? C2 C3 C7 106.41(14) . . ? C7 C3 C4 131.27(15) . . ? C3 C4 H4A 110.0 . . ? C3 C4 H4B 110.0 . . ? C3 C4 C5 108.49(13) . . ? H4A C4 H4B 108.4 . . ? C5 C4 H4A 110.0 . . ? C5 C4 H4B 110.0 . . ? C4 C5 H5 107.3 . . ? C12 C5 C4 113.29(15) . . ? C12 C5 H5 107.3 . . ? N1 C5 C4 112.81(14) . . ? N1 C5 H5 107.3 . . ? N1 C5 C12 108.54(13) . . ? C8 C6 C7 122.00(15) . . ? N2 C6 C7 108.28(14) . . ? N2 C6 C8 129.72(16) . . ? C6 C7 C3 106.83(14) . . ? C11 C7 C3 133.72(17) . . ? C11 C7 C6 119.44(16) . . ? C6 C8 H8 121.5 . . ? C9 C8 C6 117.00(18) . . ? C9 C8 H8 121.5 . . ? C8 C9 H9 119.1 . . ? C8 C9 C10 121.79(18) . . ? C10 C9 H9 119.1 . . ? C9 C10 H10 119.5 . . ? C11 C10 C9 121.02(16) . . ? C11 C10 H10 119.5 . . ? C7 C11 H11 120.6 . . ? C10 C11 C7 118.72(18) . . ? C10 C11 H11 120.6 . . ? N3 C12 C5 118.02(14) . . ? O1 C12 C5 120.38(14) . . ? O1 C12 N3 121.44(15) . . ? C1 C13 H13 108.3 . . ? C16 C13 C1 120.71(14) . . ? C16 C13 H13 108.3 . . ? N3 C13 C1 109.18(12) . . ? N3 C13 H13 108.3 . . ? N3 C13 C16 101.43(12) . . ? H14A C14 H14B 109.0 . . ? C15 C14 H14A 111.0 . . ? C15 C14 H14B 111.0 . . ? N3 C14 H14A 111.0 . . ? N3 C14 H14B 111.0 . . ? N3 C14 C15 103.78(13) . . ? C14 C15 H15A 110.6 . . ? C14 C15 H15B 110.6 . . ? H15A C15 H15B 108.7 . . ? C16 C15 C14 105.76(13) . . ? C16 C15 H15A 110.6 . . ? C16 C15 H15B 110.6 . . ? C13 C16 C15 101.61(13) . . ? C13 C16 H16A 111.4 . . ? C13 C16 H16B 111.4 . . ? C15 C16 H16A 111.4 . . ? C15 C16 H16B 111.4 . . ? H16A C16 H16B 109.3 . . ? C1 N1 C5 109.71(12) . . ? C1 N1 H1 110.6(16) . . ? C5 N1 H1 112.3(16) . . ? C2 N2 C6 107.54(13) . . ? C2 N2 H2 126.8(12) . . ? C6 N2 H2 125.6(12) . . ? C12 N3 C13 126.99(14) . . ? C12 N3 C14 121.76(13) . . ? C14 N3 C13 109.43(12) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -1 6 -1 0.1066 -1.0042 5.9964 -1.0128 0.4967 -0.5256 -0.6014 4 2 4 0.1083 3.9967 1.9976 4.0000 -0.4247 0.3634 -0.7805 -1 -6 -1 0.0856 -0.9949 -5.9959 -0.9892 -0.2242 0.2770 0.8691 -4 -1 -4 0.1032 -3.9975 -0.9982 -4.0020 0.4848 -0.4302 0.6580 -1 0 12 0.0444 -1.0051 0.0000 12.0031 -0.7510 -0.6193 -0.0290 1 0 -12 0.0281 1.0051 -0.0000 -12.0031 0.7510 0.6193 0.0290 4 -1 4 0.1130 3.9991 -1.0005 4.0059 -0.6049 0.5640 -0.4129 2 -6 2 0.1012 2.0038 -5.9967 2.0138 -0.6329 0.6498 0.4675 3 5 2 0.0951 2.9952 4.9960 1.9928 -0.0400 0.0765 -1.0017 2 6 1 0.0887 1.9949 5.9956 0.9899 0.1563 -0.1147 -0.9904